Butylated hydroxytoluene

First approved in 1984

Details

Stereochemistry	ACHIRAL
Molecular Formula	C15H24O
Molecular Weight	220.3505
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC1=CC(=C(O)C(=C1)C(C)(C)C)C(C)(C)C

InChI

InChIKey=NLZUEZXRPGMBCV-UHFFFAOYSA-N

InChI=1S/C15H24O/c1-10-8-11(14(2,3)4)13(16)12(9-10)15(5,6)7/h8-9,16H,1-7H3

HIDE SMILES / InChI

Molecular Formula	C15H24O
Molecular Weight	220.3505
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.drugs.com/inactive/butylated-hydroxytoluene-304.html | http://science.jrank.org/pages/1100/Butylated-Hydroxytoluene.html | https://www.accessdata.fda.gov/scripts/cdrh/cfdocs/cfCFR/CFRSearch.cfm?fr=172.115 | https://www.sciencedirect.com/science/article/pii/0013935182900020 | https://www.ncbi.nlm.nih.gov/pubmed/2988845

Butylated hydroxytoluene, commonly known as BHT, is an organic compound that is used in the food, cosmetic, and pharmaceutical industry as an antioxidant. BHT is a substituted derivative of phenol. BHT helps to prevent the formation of free radicals and oxidation. When used in food products, it delays oxidative rancidity of fats and oils, and prevents loss of activity of oil-soluble vitamins. It may be found in pharmaceutical gels, creams and liquid or gelatin capsules, tablets and other pharmaceutical dosage forms. The ability of oral BHT to lead to cancer is a controversial topic, but most food industries have replaced it with butylated hydroxyanisole (BHA). BHT was first used as an antioxidant food additive in 1954. BHT does have other commercial uses, as in animal feeds and in the manufacture of synthetic rubber and plastics, where it also acts as an antioxidant. The U.S. Food and Drug Administration has deemed that BHT is safe enough when used in limited concentrations. It currently permits its use in concentrations of about 0.01% to 0.02% in most foods. As an emulsion stabilizer in shortening, it may be used in a somewhat higher concentration, 200 parts per million.

CNS Activity

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Carbonic anhydrase II 88 Target ID: CHEMBL205 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19231207	Inhibitor 8504		630.0 nM [Ki]
Oxidative Stress 162 Target ID: WP408 Sources: https://www.ncbi.nlm.nih.gov/pubmed/29295625 \| https://www.ncbi.nlm.nih.gov/pubmed/29205116 \| https://www.drugs.com/inactive/butylated-hydroxytoluene-304.html	Inhibitor 8504

Conditions

Condition	Modality	Highest Phase	Product
Asthma 244 Sources: https://clinicaltrials.gov/ct2/show/NCT02220673	Primary	Phase I 438	Unknown Approved Use Unknown
Herpes simplex infection 28 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2988845 https://www.webmd.com/vitamins-supplements/ingredientmono-1071-butylated%20hydroxytoluene.aspx?activeingredientid=1071&activeingredientname=butylated%20hydroxytoluene	Primary	Phase I 438	Unknown Approved Use Unknown
SUNBURN 11 Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=f6db0332-58ed-4c82-a9dc-7fac621f1ac1	Inactive ingredient	Approved 8583	A-TEAM Approved Use USE HELPS PROTECT AGAINST SUNBURN Launch Date 2014

C_max

Value	Dose	Co-administered	Analyte	Population
0.09 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2606406/	0.5 mg/kg bw single, oral dose: 0.5 mg/kg bw route of administration: Oral experiment type: SINGLE co-administered:		BUTYLATED HYDROXYTOLUENE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN

AUC

Value	Dose	Co-administered	Analyte	Population
76 μg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2606406/	0.5 mg/kg bw single, oral dose: 0.5 mg/kg bw route of administration: Oral experiment type: SINGLE co-administered:		BUTYLATED HYDROXYTOLUENE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN

Doses

Dose	Population	Adverse events
15 % 4 times / day multiple, topical Highest studied dose Dose: 15 %, 4 times / day Route: topical Route: multiple Dose: 15 %, 4 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/2988845/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/2988845/	Sources: https://pubmed.ncbi.nlm.nih.gov/2988845/
80 g single, oral Overdose Dose: 80 g Route: oral Route: single Dose: 80 g Sources: https://pubmed.ncbi.nlm.nih.gov/3765608/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: F Food Status: FASTED Sources: https://pubmed.ncbi.nlm.nih.gov/3765608/	Other AEs: Dysarthria, Lightheadedness... Other AEs: Dysarthria Lightheadedness Abnormality of gait Slurred speech Sources: https://pubmed.ncbi.nlm.nih.gov/3765608/

AEs

AE	Dose	Population
Abnormality of gait	80 g single, oral Overdose Dose: 80 g Route: oral Route: single Dose: 80 g Sources: https://pubmed.ncbi.nlm.nih.gov/3765608/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: F Food Status: FASTED Sources: https://pubmed.ncbi.nlm.nih.gov/3765608/
Dysarthria	80 g single, oral Overdose Dose: 80 g Route: oral Route: single Dose: 80 g Sources: https://pubmed.ncbi.nlm.nih.gov/3765608/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: F Food Status: FASTED Sources: https://pubmed.ncbi.nlm.nih.gov/3765608/
Lightheadedness	80 g single, oral Overdose Dose: 80 g Route: oral Route: single Dose: 80 g Sources: https://pubmed.ncbi.nlm.nih.gov/3765608/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: F Food Status: FASTED Sources: https://pubmed.ncbi.nlm.nih.gov/3765608/
Slurred speech	80 g single, oral Overdose Dose: 80 g Route: oral Route: single Dose: 80 g Sources: https://pubmed.ncbi.nlm.nih.gov/3765608/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: F Food Status: FASTED Sources: https://pubmed.ncbi.nlm.nih.gov/3765608/

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inducer 1087 inhibitor 2252	inhibitor 2438	inhibitor 2507	inhibitor 2217

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
BCRP 910 P-gp 1741 CYP19A1 429 CYP1A2 2153 UMAT 30 CYP2C19 2057 rGSTA5 1	rCYP 3 UGT1A6 343 UGT1A9 423	CYP2B6 669

Drug as perpetrator

Target	Modality	Activity
CYP1A2 2333	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/bioassay/1671199#sid=170466785	inconclusive [IC50 27.5404 uM]
CYP2D6 2546	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/bioassay/1671196#sid=144208291	inconclusive [IC50 40.0452 uM]
CYP19A1 430	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/bioassay/743083#sid=144213719	inconclusive [IC50 43.2771 uM]
CYP3A4 2633	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/bioassay/1671201#sid=144208291	inconclusive [IC50 44.9314 uM]
BCRP 985	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/bioassay/1325#sid=11532869	no
P-gp 1932	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/bioassay/1326#sid=11532869	no
UMAT 30	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/bioassay/1326#sid=11532869	no
CYP2C9 2497	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/bioassay/1671198#sid=144208291	yes [IC50 35.6903 uM]
CYP2B6 1160	inducer 1966 Sources: https://pubmed.ncbi.nlm.nih.gov/18570159/	yes
CYP2C19 2141	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/22931300/	yes
CYP3A4 2633	inducer 1966 Sources: https://pubmed.ncbi.nlm.nih.gov/18570159/	yes
rGSTA5 1	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/8923030/	yes

Drug as victim

Target	Modality	Activity
UGT1A6 343	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/10836148/	no
UGT1A9 423	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/10836148/	no
rCYP 3	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/3473001/	yes

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 2263	inhibitor 2237 Sources: https://pubchem.ncbi.nlm.nih.gov/bioassay/588834#sid=17390001

PubMed

Title	Date	PubMed
Elastin gene expression is upregulated during pulmonary fibrosis.	1999	10761639
Nrf2 is essential for protection against acute pulmonary injury in mice.	1999 Oct 26	10535991
Chemoprevention of heterocyclic amine-induced carcinogenesis by phenolic compounds in rats.	1999 Sep 1	10503899
Examination of selected food additives and organochlorine food contaminants for androgenic activity in vitro.	2000 Feb	10696776
Differential expression and localization of the mRNA binding proteins, AU-rich element mRNA binding protein (AUF1) and Hu antigen R (HuR), in neoplastic lung tissue.	2000 Jun	10900464
Glycation amplifies lipoprotein(a)-induced alterations in the generation of fibrinolytic regulators from human vascular endothelial cells.	2000 Jun	10856522
Direct interaction of GD3 ganglioside with mitochondria generates reactive oxygen species followed by mitochondrial permeability transition, cytochrome c release, and caspase activation.	2000 May	10783138
MAP: microwave-assisted extraction of fatty acids and Py/GC/MS analysis of selected insects.	2001	11858551
Detection of estrogenicity by bioassay on the mouse mammary gland in vivo.	2001	11521738
Differential expression of forkhead box transcription factors following butylated hydroxytoluene lung injury.	2001 Apr	11238010
Thermochemical and kinetic studies of a bisphenol antioxidant.	2001 Aug 10	11485470
The lung tumor promoter, butylated hydroxytoluene (BHT), causes chronic inflammation in promotion-sensitive BALB/cByJ mice but not in promotion-resistant CXB4 mice.	2001 Dec 1	11696405
Estrogenic activity of phenolic additives determined by an in vitro yeast bioassay.	2001 Feb	11266322
Separation of hydrophobic polymer additives by microemulsion electrokinetic chromatography.	2001 Jul 13	11486875
In vitro test for the effectiveness of antioxidants as inhibitors of thiyl radical-induced reactions with unsaturated fatty acids.	2001 Mar	11312840
Studies using structural analogs and inbred strain differences to support a role for quinone methide metabolites of butylated hydroxytoluene (BHT) in mouse lung tumor promotion.	2001 Mar 7	11246140
Heteropteris aphrodisiaca O. Machado : effects of extract BST 0298 on the oxidative stress of young and old rat brains.	2001 Nov	11746842
Butylhydroxytoluene (BHT) increases susceptibility of transgenic rasH2 mice to lung carcinogenesis.	2001 Oct	11599794
Lung toxicity and tumor promotion by hydroxylated derivatives of 2,6-di-tert-butyl-4-methylphenol (BHT) and 2-tert-butyl-4-methyl-6-iso-propylphenol: correlation with quinone methide reactivity.	2002 Aug	12184795
Practical synthesis of chiral emopamil left hand as a bioactive motif.	2002 Aug 23	12182667
Ammonia-induced heme oxygenase-1 expression in cultured rat astrocytes and rat brain in vivo.	2002 Dec	12420312
[Determination of 2,6-di-tertbutyl-4-methylphenol in an aviation jet fuel by high performance liquid chromatography].	2002 Jul	12541930
Hydrogen bonding between phenols and fatty acid esters: (1)H NMR study and ab initio calculations.	2002 Jul 11	12098263
Celecoxib reduces pulmonary inflammation but not lung tumorigenesis in mice.	2002 Oct	12376474
The uptake of tocopherols by RAW 264.7 macrophages.	2002 Oct 15	12537596
Cholesterol oxidation: health hazard and the role of antioxidants in prevention.	2003	14631863
Control of Clostridium perfringens germination and outgrowth by buffered sodium citrate during chilling of roast beef and injected pork.	2003 Mar	12636288
Reactive oxygen species mediate the down-regulation of mitochondrial transcripts and proteins by tumour necrosis factor-alpha in L929 cells.	2003 Mar 1	12470298
Effects of dietary butylated hydroxytoluene on aflatoxin B1-relevant metabolic enzymes in turkeys.	2003 May	12659720
Radical-scavenging activity of butylated hydroxytoluene (BHT) and its metabolites.	2004 Jul	15172835
Inactivation of endoplasmic reticulum bound Ca2+-independent phospholipase A2 in renal cells during oxidative stress.	2004 Jun	15153555
Vanadium-catalyzed sulfenylation of indoles and 2-naphthols with thiols under molecular oxygen.	2004 Oct 29	15497997
Synthesis, biological evaluation and molecular modelling studies on benzothiadiazine derivatives as PDE4 selective inhibitors.	2005 Feb 15	15670947
Synthesis and characterization of BHT-derived tert-butyl dendrons.	2005 Feb 4	15675869
TNF alpha potentiates glutamate neurotoxicity by inhibiting glutamate uptake in organotypic brain slice cultures: neuroprotection by NF kappa B inhibition.	2005 Feb 9	15713255
Identification and antioxidant potential of flavonoids and low molecular weight phenols in olive cultivar chemlali growing in Tunisia.	2005 Jan 26	15656655
Single-site anionic polymerization. Monomeric ester enolaluminate propagator synthesis, molecular structure, and polymerization mechanism.	2005 Jan 26	15656635
Quantitative determination of volatile organic compounds in indoor dust using gas chromatography-UV spectrometry.	2005 Oct	15936080
New analogues of butylated hydroxytoluene as anti-inflammatory and antioxidant agents.	2006 Aug 15	16690318
Enhancement of tumor invasion depends on transdifferentiation of skin fibroblasts mediated by reactive oxygen species.	2006 Jul 1	16757516
Cytokine response to lipoprotein lipid loading in human monocyte-derived macrophages.	2006 Jun 26	16800873
Does immune stimulation or antioxidant therapy reduce MNU-induced placental damage via activation of Jak-STAT and NFkappaB signaling pathways?	2007 May-Jun	16822543

Patents

Sample Use Guides

In Vivo Use Guide

The effect of topical therapy with 15% Butylated hydroxytoluene in mineral oil on the course of recurrent herpes simplex labialis was examined in 30 patients in a double-blind, placebo-controlled pilot study.

Route of Administration: Topical

In Vitro Use Guide

Butylated hydroxytoluene (BHT) inhibited lipoprotein oxidation by IC50 values of 0.8 uM

Substance Class	Chemical Created by `admin` on `Mon Mar 31 17:47:35 GMT 2025` Edited by `admin` on `Mon Mar 31 17:47:35 GMT 2025`
Record UNII	1P9D0Z171K
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

Butylated hydroxytoluene

Common Name

English

BHT	Locators: FCC INCI Naming Organization: INCI Sources:

Preferred Name

English

Butylated hydroxytoluene [WHO-DD]

Common Name

English

BUTYLATED HYDROXYTOLUENE [USP-RS]

Common Name

English

INS NO.321

Code

English

BUTYLATED HYDROXYTOLUENE [II]

Common Name

English

BUTYLHYDROXYTOLUENE [EP MONOGRAPH]

Common Name

English

E-321

Code

English

PHENOL, 2,6-BIS(1,1-DIMETHYLETHYL)-4-METHYL-

Systematic Name

English

BUTYLATED HYDROXYTOLUENE [VANDF]

Common Name

English

BUTYLATED HYDROXYTOLUENE (E 321)

Common Name

English

BUTYLATED HYDROXYTOLUENE [FHFI]

Common Name

English

BUTYLHYDROXYTOLUENE

Systematic Name

English

2,6-BIS(1,1-DIMETHYLETHYL)-4-METHYLPHENOL

Systematic Name

English

BUTYLATED HYDROXYTOLUENE [IARC]

Common Name

English

BUTYLATED HYDROXYTOLUENE [MART.]

Common Name

English

BHT [FCC]

Common Name

English

2,6-DI-TERT-BUTYL-P-CRESOL

Common Name

English

KERABIT

Common Name

English

BUTYLATED HYDROXYTOLUENE [NF]

Common Name

English

4-METHYL-2,6-DITERTIARY-BUTYL-PHENOL

Common Name

English

2,6-DI-TERT-BUTYL-P-CRESOL2,6-BIS(1,1-DIMETHYLETHYL)-4-METHYL-PHENOL

Systematic Name

English

NSC-6347

Code

English

BUTYLATED HYDROXYTOLUENE [HSDB]

Common Name

English

FEMA NO. 2184

Code

English

BUTYLATED HYDROXYTOLUENE [MI]

Common Name

English

INS-321

Code

English

2,6-DITERTIARY-BUTYL-P-CRESOL

Common Name

English

BUTYLATED HYDROXYTOLUENE [WHO-IP]

Common Name

English

BUTYLHYDROXYTOLUENUM [WHO-IP LATIN]

Common Name

English

Classification Tree Code System Code

EPA PESTICIDE CODE

22105